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Posted August 23, 2026

Senior Systems Engineer

359557 Trivail LLC
Chicago, IL, US Full Time
75000USD - 90000USD per year

Job Description

Job Description
Description:

Job Summary

We are seeking a highly skilled and experienced Senior Systems Engineer to join our dynamic team. The ideal candidate will possess a deep understanding of systems engineering principles and be proficient in designing, implementing, and managing complex IT infrastructures. This role requires expertise in service-oriented architecture, system performance, and security.

Requirements:

Client & Team Support

  • Provide leadership, support, and supplementation to Junior Systems Administrators and Helpdesk Technicians
  • Oversee and complete support queue requests to ensure SLAs are being met
  • Serve as a client's highest point of contact for technical matters and service thereof
  • Resolve system performance and connectivity issues
  • Available to manage occasional escalations outside standard business hours; such instances are rare but should be expected as part of the role

Infrastructure & Systems Management

  • Configure and deploy new servers and services and perform upgrades as needed
  • Participate in the design, deployment, and management of diverse server infrastructure deployments
  • Advanced technical knowledge of current network protocols and standards, including Windows 10/11 (desktop/laptop)
  • Advanced technical knowledge of Windows Server 2012 R2 through Server 2022
  • Advanced technical knowledge of Mac OS X environments
  • Advanced understanding of Microsoft-specific technologies including Active Directory, DFS, Exchange, MSSQL, and Hyper-V
  • Managing Microsoft cloud and on-prem technologies including Office 365 (Intune, Exchange, OneDrive/SharePoint, Teams, Defender), Azure services (Entra ID, DNS, VPN, VM, Backups)
  • Familiarity with Synology devices and backup/retention solutions such as Veeam and Backblaze B2
  • Familiarity with the configuration/management of Juniper network equipment
  • Exposure to WSL/Linux is a plus
  • Write PowerShell scripts for information gathering, management, and deployment of systems

Security & Documentation

  • Monitor system performance and enforce security best practices
  • Research and propose technical solutions, offerings and strategy to management
  • Lead project documentation, status reporting, and internal/external communication
  • Maintain project plans and provide escalation to management as needed

Qualifications

  • Bachelor’s degree in computer science or a related field; an advanced degree is a plus.
  • Proven experience in systems engineering with a strong focus on system architecture design.
  • Experience with cloud platforms such as AWS or Azure is essential.
  • Strong understanding of computer networking concepts, including DNS, VPNs, firewalls, and general networking techniques.
  • Strong analytical skills with the ability to debug complex systems effectively.
  • 5+ years of experience in systems engineering or administration
  • Strong oral and written communication skills
  • Emphasis on ethics, accountability, and documentation discipline
  • Desire to pursue ongoing certifications and technical development

Job Type:

  • Full-time

Benefits:

  • 401(k) Retirement plan
  • 401(k) matching
  • Dental insurance
  • Vision insurance
  • Flexible schedule
  • Health insurance
  • Health savings account
  • Life insurance
  • Short Term Disability
  • Paid time off

Work Location:

This is a home-based Hybrid role — we do not maintain a company office. Candidates must reside in the Chicagoland Area, as the role requires travel to Hodgkins, IL and nearby client sites. Chicagoland Area — with travel to Hodgkins, IL and nearby client sites

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